$96+ Cheap flights from Chicago (CHI) to Winnipeg (YWG)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Chicago to Winnipeg with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Winnipeg
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Winnipeg (YWG). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $283 (Kiwi.com) |
One-way from | $96 (Kiwi.com) |
Popular in | April |
Cheapest in | January |
Average price | $319 |
Good round-trip deal | $226 or less |
Find flight deals from Chicago to Winnipeg
Cheapest flights from Chicago to WinnipegExplore the most affordable flight options available from Chicago to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2025.
Explore the most affordable flight options available from Chicago to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2025.
This Kiwi.com deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Mytrip deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Justfly.com deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Air Canada deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Gotogate deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This United Airlines deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This WestJet deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Find flights from Chicago to Winnipeg within your budget
Customize your flight search to find flights from Chicago to Winnipeg that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 21, 2025.
Fly from
Fly to
Route
Depart
Return
Price
ChicagoWinnipeg
MDW - YWG
MDWYWG
Chicago Midway
Fri 3/7
6:20 am-3:08 pm
1 stop8h 48m
Winnipeg
Fri 3/14
7:30 am-11:58 pm
1 stop16h 28m
ChicagoWinnipeg
ORD - YWG
ORDYWG
Chicago O'Hare Intl
Tue 2/18
11:35 am-3:08 pm
2 stops27h 33m
Winnipeg
Tue 2/25
7:30 am-11:58 pm
2 stops16h 28m
ChicagoWinnipeg
ORD - YWG
ORDYWG
Chicago O'Hare Intl
Fri 3/7
7:30 am-3:08 pm
1 stop7h 38m
Winnipeg
Fri 3/14
11:55 am-7:18 am
2 stops19h 23m
ChicagoWinnipeg
ORD - YWG
ORDYWG
Chicago O'Hare Intl
Fri 2/21
8:25 pm-11:18 am
1 stop14h 53m
Winnipeg
Sun 2/23
12:15 pm-7:37 pm
1 stop7h 22m
ChicagoWinnipeg
MDW - YWG
MDWYWG
Chicago Midway
Tue 3/4
11:15 am-6:04 pm
2 stops30h 49m
Winnipeg
Tue 3/18
11:35 am-10:20 am
2 stops22h 45m
ChicagoWinnipeg
ORD - YWG
ORDYWG
Chicago O'Hare Intl
Tue 3/4
12:58 pm-3:28 pm
Nonstop2h 30m
Winnipeg
Tue 3/18
2:15 pm-4:37 pm
Nonstop2h 22m
ChicagoWinnipeg
ORD - YWG
ORDYWG
Chicago O'Hare Intl
Tue 2/18
6:45 am-4:43 pm
2 stops9h 58m
Winnipeg
Tue 2/25
6:40 am-3:30 pm
1 stop8h 50m
ChicagoWinnipeg
MDW - YWG
MDWYWG
Chicago Midway
Wed 3/5
10:19 am-4:43 pm
1 stop6h 24m
Winnipeg
Wed 3/12
6:50 am-2:15 pm
1 stop7h 25m
ChicagoWinnipeg
MDW - YWG
MDWYWG
Chicago Midway
Fri 2/21
2:08 pm-11:22 am
2 stops21h 14m
Winnipeg
Sun 2/23
5:37 pm-5:43 pm
1 stop24h 06m
ChicagoWinnipeg
MDW - YWG
MDWYWG
Chicago Midway
Mon 3/3
6:48 pm-3:08 pm
1 stop20h 20m
Compare providers for flights from Chicago to Winnipeg
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Winnipeg in January.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Winnipeg flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Winnipeg flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Winnipeg flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Winnipeg flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Winnipeg flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Chicago to Winnipeg
Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Chicago with our price prediction graph.
Travel insights for flights from Chicago to Winnipeg
Get recent, data-driven insights about flights from Chicago to Winnipeg including ideal travel times, pricing trends, and more.
What is the cheapest month to book a flight from Chicago to Winnipeg?
Currently, August is the cheapest month in which you can book a flight from Chicago to Winnipeg (average of $358). Flying from Chicago to Winnipeg in February is currently the most expensive (average of $521). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to YWG?
Find hourly flight availability from Chicago to Winnipeg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 21, 2025.
One of the essential ways to save on airfare from Chicago to Winnipeg is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the morning could potentially save you up to 18% on airfare.
What is the cheapest day to fly from Chicago to Winnipeg?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Winnipeg. Price data was last updated on December 16, 2024.
Travelers seeking maximum savings on their Chicago to Winnipeg flight should consider departing on Thursday mornings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Chicago to Winnipeg
Explore weekly flight availability from Chicago to Winnipeg. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated January 21, 2025.
The most flights from CHI to YWG are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 on average).
Rainfall in Winnipeg by month
Plan your trip to Winnipeg by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Winnipeg ranges from 0.8 - 3.1 inches per month. June is typically the wettest month, when rainfall can reach 3.1 in. January is typically the driest time to visit Winnipeg when rainfall is around 0.8 in.
Temperature in Winnipeg by month
Plan your trip to Winnipeg by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Winnipeg, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 3.2 F).
Reviews of airlines servicing Winnipeg
Get insights into the airlines that provide service to Winnipeg. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Winnipeg. Reviews last updated January 21, 2025.
See what other customers who have flown with WestJet, Air Canada and Delta from Chicago to Winnipeg have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
Comfort
Crew
Boarding
Entertainment
Overall
Reviews
This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Food
Comfort
Crew
Boarding
Entertainment
Overall
Reviews
This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Food
Comfort
Crew
Boarding
Entertainment
Overall
Reviews
This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Food
Comfort
Crew
Boarding
Entertainment
Overall
Reviews
This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Food
Comfort
Crew
Boarding
Entertainment
Overall
Reviews
This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Food
Comfort
Crew
Boarding
Entertainment
Overall
Reviews
This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Related info for your journey
Find useful and relevant information for your journey from Chicago to Winnipeg. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes for Chicago to Winnipeg
See prices for flight routes from nearby airports that may be better suited for you.
Top 3 airlines flying from Chicago to Winnipeg
Discover the top 3 airlines that operate flights from Chicago to Winnipeg. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 21, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$235 | Average$592 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$510 | Average$636 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$535 | Average$703 | FlexibilityNo cancel fee | On-time69% |